Pyridine → HCID 86644694, compound

HRID 1097494Notes

Reaction equation

HRID 1097494 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]#[N:12])=[C:9]([O:13][C:14]3[CH:15]=[CH:16][C:17]([F:27])=[C:18]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:19]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[C:34](Cl)(=[O:36])[CH3:35]>O1CCCC1.C(OCC)(=O)C>[C:34]([NH:1][C:2]1[S:3][C:4]2[C:10]([C:11]#[N:12])=[C:9]([O:13][C:14]3[CH:15]=[CH:16][C:17]([F:27])=[C:18]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:23])[F:24])[CH:19]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 71819024HCID 71819024, compound

Product 1

HCID 86644694HCID 86644694, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{5-[(2-amino-7-cyano-1,3-benzothiazol-6-yl)oxy]-2-fluorophenyl}-2,2,2-trifluoroacetamide (1.5 g, 3.78 mmol) produced in Example 30 (iv) in tetrahydrofuran (20 mL) were added pyridine (20 mL) and acetyl chloride (403 μL, 5.67 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (300 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (150 mL) and saturated brine (150 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=30/70→100/0), and the obtained solution was concentrated under reduced pressure to give the title compound (740 mg, 45%) as a white powder.

Workup

  1. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (150 mL) and saturated brine (150 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=30/70→100/0)
  6. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d445b63072074e0ebf17fbe952b6a9be
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

Loading…